N-Iodosuccinimide → tert-Butyl 2-(9-iodo-7-(4-Isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

Participants

Reaction Steps

To a solution of tert-butyl 2-(7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (0.722 g, 1.434 mmol) in DCM (24 mL) at 0° C. was added NIS (1.434 mmol). After 5 minutes, the reaction was diluted with DCM and washed with water (twice) and saturated sodium thiolsulfate (aq). The organics were dried over Na2SO4, filtered, and concentrated to give the title compound as a light-brown solid. LCMS m/z=630.5 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.29 (d, J=6.06 Hz, 6H), 1.38 (s, 9H), 2.27-2.38 (m, 1H), 2.51-2.56 (m, 1H), 2.77-2.89 (m, 1H), 2.94 (dd, J=15.92, 3.41 Hz, 1H), 3.51-3.61 (m, 1H), 3.99-4.09 (m, 1H), 4.12-4.21 (m, 1H), 4.74-4.83 (m, 1H), 5.10 (s, 2H), 6.78 (d, J=2.27 Hz, 1H), 6.85 (dd, J=8.72, 2.40 Hz, 1H), 7.25 (d, J=8.84 Hz, 1H), 7.30 (d, J=8.34 Hz, 1H), 7.66-7.73 (m, 2H).

Provenance & Evidence